About Sales Ask

Sales Ask is an AI-powered sales coaching platform that transforms real customer conversations into revenue-driving insights. By recording, transcribing, and analyzing in-person sales interactions, SalesAsk helps teams execute better, close more deals, and scale winning behaviors across every rep. Role overview

We're looking for a driven and customer-focused Senior Customer Success Manager to own relationships end-to-end from onboarding through ongoing customer management. You'll work directly with customers to get them live quickly, drive platform adoption, and help them improve sales performance. You'll be highly visible, deeply embedded in their outcomes, and a key driver of retention and growth.

You'll also help us build how Customer Success operates as we scale — this is a foundational role. What you'll do

Own the full customer lifecycle — onboarding through ongoing management

Lead onboarding calls and get customers live quickly

Train customers on how to use SalesAsk to drive real results

Run customer trainings and webinars

Act as the main point of contact — answer questions and guide usage

Drive adoption and engagement across accounts

Identify risks early and help reduce churn

Identify and surface upsell and seat expansion opportunities

Maintain strong follow-up and communication with customers

Capture feedback and help improve the customer experience

Help build processes, playbooks, and customer-facing content What we're looking for

5+ years in Customer Success, Account Management, or similar





Strong communication skills and confidence working directly with customers

Comfortable owning relationships end-to-end

Customer-focused mindset — you care about outcomes, not just activity

High ownership and urgency — you follow through and don't let things drop

Comfortable with high-touch, high-volume customer interaction

Able to manage multiple accounts in a fast-paced environment

Comfortable identifying growth opportunities within accounts

Excited to build and improve processes, not just follow them

Comfortable with ambiguity and figuring things out as you go This role is not for someone who wants a highly structured environment or a narrow scope — you'll be building as you go. We hire for attitude, ownership, and coachability — we'll support you on the rest. What success looks like

Customers get live quickly and actively use the platform

Strong relationships and consistent engagement across accounts

Early identification and reduction of churn risk

Expansion opportunities identified and surfaced across your book

High customer satisfaction and retention Why join SalesAsk

Fast-growing AI company with robust market demand

High-impact role with direct visibility into customer outcomes

Opportunity to help build Customer Success from the ground up

Clear growth opportunities as the team scales

High-performance, ownership-driven culture

Remote-first team A team that celebrates wins — big and small If this sounds like you - we'd love to hear from you!

📌 Senior Customer Success Manager (Canada)
🏢 SalesAsk
📍 Canada